bis((2S,5R)-5-amino-2-benzyl-8-carbamimidamido-4-oxooctanoic acid); sulfuric acid

• ChemBase ID: 133040
• Molecular Formular: C32H50N8O10S
• Molecular Mass: 738.852
• Monoisotopic Mass: 738.33706084
• SMILES: c1ccc(cc1)C[C@@H](CC(=O)[C@@H](CCCNC(=N)N)N)C(=O)O.c1ccc(cc1)C[C@@H](CC(=O)[C@@H](CCCNC(=N)N)N)C(=O)O.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.NC(=N)NCCC[C@H](C(=O)C[C@@H](C(=O)O)Cc1ccccc1)N.NC(=N)NCCC[C@H](C(=O)C[C@@H](C(=O)O)Cc1ccccc1)N
• InChI: InChI=1S/2C16H24N4O3.H2O4S/c2*17-13(7-4-8-20-16(18)19)14(21)10-12(15(22)23)9-11-5-2-1-3-6-11;1-5(2,3)4/h2*1-3,5-6,12-13H,4,7-10,17H2,(H,22,23)(H4,18,19,20);(H2,1,2,3,4)/t2*12-,13+;/m00./s1
• InChIKey: MOKRJPVCHKXEMO-FFOUBCEFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((2S,5R)-5-amino-2-benzyl-8-carbamimidamido-4-oxooctanoic acid); sulfuric acid
• IUPAC Traditional name: bis((2S,5R)-5-amino-2-benzyl-8-carbamimidamido-4-oxooctanoic acid); sulfuric acid
• Synonyms: (2R,5S)-5-Amino-8-guanido-4-oxo-2-phenylmethyloctanoic Acid; Arphamenine A hemisulfate salt

Database IDs

• CAS Number: 144110-37-2
• MDL Number: MFCD00135887
• PubChem SID: 24890645; 162227317
• PubChem CID: 71308623

CALCULATED PROPERTIES

• Acid pKa: 4.18039
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -3.0686736
• LogD (pH = 7.4): -1.3739327
• Log P: -0.86429626
• Molar Refractivity: 97.638 cm^3
• Polarizability: 33.87086 Å^3
• Polar Surface Area: 142.29 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Biological Source: from microbial

DETAILS

Sigma Aldrich - A2302

Biochem/physiol Actions
Potent inhibitor of aminopeptidase B and of the suite of enkephalin-degrading peptidases.